Aryl sulfonamides as effective analgesics   

The present invention relates to compounds of general formula I

wherein A, B, R1, R2 and R3 are defined as hereinafter, the enantiomers, the diastereomers, the mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases, which have valuable properties, the preparation thereof, the pharmaceutical compositions containing the pharmacologically effective compounds, the preparation thereof and the use thereof.

DETAILED DESCRIPTION

In the above general formula I in a first embodiment

A denotes (a) a bond or (b) a C1-3-alkylene group, B denotes (a) a bond, (b) a C1-3-alkylene or (c) a —C(O)— group, R1 denotes (a) H, (b) C1-3-alkyl, (c) C3-6-cycloalkyl, (d) a 5- or 6-membered, saturated aza-heterocycle or (e) a 5- or 6-membered, saturated oxa-heterocycle, R2 denotes (a) C1-3-alkylene, (b) a 4- to 6-membered, saturated aza-heterocycle, or (c) a 6- to 7-membered, saturated diaza-heterocycle, R3 denotes (a) C2-4-alkenylene, (b) C2-4-alkynylene or (c) a 5- to 6-membered, saturated aza-heterocycle, wherein additionally a methylene group may be substituted by a carbonyl group, the enantiomers, the diastereomers, the mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases.

A second embodiment of the present invention comprises the compounds of the above general formula I, wherein

A denotes a bond or a —CH2— group, B denotes a bond, a —CH2— or —C(O)— group, R1 denotes H, H3C— or a group selected from

R2 denotes a group selected from

and R3 denotes a group selected from

the enantiomers, the diastereomers, the mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases.

The following are mentioned as examples of most particularly preferred compounds of the above general formula I:

Example Structure  (1)  (2)  (3)  (4)  (5)  (6)  (7)  (8)  (9) (10) (11) (12) (13) the enantiomers, the diastereomers, the mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases.

Within the scope of this application, in the definition of possible substituents, these may also be represented in the form of a structural formula. If present, an asterisk (*) in the structural formula of the substituent is to be understood as being the linking point to the rest of the molecule.

The subject-matter of this invention also includes the compounds according to the invention, including the salts thereof, wherein one or more hydrogen atoms, for example one, two, three, four or five hydrogen atoms, are replaced by deuterium.

By the term “C1-3-alkyl” (including those which are part of other groups) are meant alkyl groups with 1 to 3 carbon atoms. Examples include: methyl, ethyl, n-propyl and iso-propyl. The following abbreviations may also optionally be used for the above-mentioned groups: Me, Et, n-Pr or i-Pr. Unless stated otherwise, the definition propyl includes all the possible isomeric forms of the group, such as, for example, propyl, n-propyl and iso-propyl.

Moreover, the terms mentioned above also include those groups wherein each methylene group may be substituted by up to two fluorine atoms and each methyl group may be substituted by up to three fluorine atoms.

By the term “C1-3-alkylene” are meant branched and unbranched alkylene groups with 1 or 3 carbon atoms. Examples include: methylene, ethylene, ethan-1,1-diyl and propylene. Unless stated otherwise, the definition propylene encompasses all the possible isomeric forms with the same number of carbons, for example 1-methylethylene.

Moreover, the terms mentioned above also include those groups wherein each methylene group may be substituted by up to two fluorine atoms.

By the term “C2-4-alkenylene” (including those which are part of other groups) are meant branched and unbranched alkenylene groups with 2 to 4 carbon atoms. Examples include: ethenylene, propenylene, 1-methylethenylene, butenylene, 1-methylpropenylene, 1,1-dimethylethenylene or 1,2-dimethylethenylene. Unless stated otherwise, the definitions propenylene and butenylene include all the possible isomeric forms of the groups in question with the same number of carbons. Thus, for example, propenyl also includes 1-methylethenylene and butenylene includes 1-methylpropenylene, 1,1-dimethylethenylene, 1,2-dimethylethenylene.

By the term “C2-4-alkynylene” (including those which are part of other groups) are meant branched and unbranched alkynylene groups with 2 to 4 carbon atoms. Examples include: ethynylene, propynylene, 1-methylethynylene, butynylene, 1-methylpropynylene, 1,1-dimethylethynylene or 1,2-dimethylethynylene. Unless stated otherwise, the definitions propynylene and butynylene include all the possible isomeric forms of the groups in question with the same number of carbons. Thus, for example, propynyl also includes 1-methylethynylene and butynylene includes 1-methylpropynylene, 1,1-dimethylethynylene, 1,2-dimethylethynylene.

By the term “C3-6-cycloalkyl” (including those which are part of other groups) are meant cyclic alkyl groups with 3 to 6 carbon atoms. Examples include: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Unless otherwise stated, the cyclic alkyl groups may be substituted by one or more groups selected from among methyl, ethyl, iso-propyl, tert-butyl, hydroxy, fluorine, chlorine, bromine and iodine.

By the term “saturated aza-heterocycles” are meant four-, five- or six-membered heterocyclic rings which contain a nitrogen atom. The ring is attached to the rest of the molecule either through the nitrogen atom or through the nitrogen atom and a carbon atom. Examples include:

By the term “saturated diaza-heterocycles” are meant six- or seven-membered heterocyclic rings which contain two nitrogen atoms. The ring is attached to the rest of the molecule through the two nitrogen atoms. Examples include:

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